Among the conventional manufacturing methods of 4,4″-dihydroxy-m-terphenyl, a method is disclosed, for example, whereby a 4,4″-dihydroxy-m-terphenyl is synthesized by causing a 1,1,3,3-tetrakis(4-hydroxyphenyl)-cyclohexane, which has been synthesized from 1,3-cyclohexane dione and phenol, to undergo breakdown and dehydrogenation reactions (Patent Literature 1). With this method, however, the yield of material tetrakis phenol is extremely low or material tetrakis phenol cannot be synthesized at all.
Also disclosed is a method to synthesize a 4,4″-dihydroxy-m-terphenyl by causing 2-(4-bromophenoxyl)tetrahydro-2H-pyrane and 1,3-dibromobenzene to undergo Grignard reaction, followed by deprotection (Patent Literature 2); and by causing 4-methoxyphenyl boronic acid to react with 1,3-diiodobenzene, followed by deprotection (Patent Literature 3), respectively.
However, these methods are associated with very high manufacturing cost and thus difficult to implement in industrial settings, because special, expensive materials such as organic metal compounds are used and Grignard reaction, etc., must be implemented.
On the other hand, a method to manufacture a dihydroxy-p-terphenyl from a trisphenol is also known (Patent Literature 4), but there is no mention, in this patent literature, of how a trisphenol is manufactured from an unsaturated ketone or how a dihydroxy-m-terphenyl is manufactured.